This is 54: Cheryl Strayed Responds to The Oldster Magazine Questionnaire
"Fifty-four years of living has taught me that I can persist through the hard times—and also that hard times pass."
From the time I was 10, I’ve been obsessed with what it means to grow older. I’m curious about what it means to others, of all ages, and so I invite them to take “The Oldster Magazine Questionnaire.”
Here, acclaimed author and advice columnist responds.
***Tomorrow night, Friday, April 7th, Hulu launches Tiny Beautiful Things starring Kathryn Hahn—a show based on and Strayed’s recently reissued advice collection, Tiny Beautiful Things: Advice from Dear Sugar. Don’t miss it!***
-Sari Botton
is the author of the #1 New York Times bestseller Wild: From Lost to Found on the Pacific Crest Trail, which has sold more than 4 million copies worldwide and was made into an Oscar-nominated film. In 2023, her bestselling collection of Dear Sugar columns, Tiny Beautiful Things, was adapted for a Hulu television show and in 2016, it was adapted as a play that continues to be staged in theaters around the world. Strayed is also the author of the critically acclaimed novel, Torch, and the bestselling collection Brave Enough, which brings together more than one hundred of her inspiring quotes. Her award-winning essays and stories have appeared in The Best American Essays, the New York Times, Vogue, The Sun Magazine and elsewhere. Strayed has also made two hit podcasts—Dear Sugars, which she co-hosted with Steve Almond, and Sugar Calling. She lives in Portland, Oregon.
How old are you?
54.
Is there another age you associate with yourself in your mind? If so, what is it? And why, do you think?
No.
Do you feel old for your age? Young for your age? Just right? Are you in step with your peers?
I feel my age now, but that’s a fairly recent thing. I felt old for my age for most of my life—from my teenage years until I hit my mid-40s. When I went to college at the age of 17 I became financially independent—it wasn’t that my mom didn’t want to support me. It was that she couldn’t. Most of my college peers were mystified that I was working three jobs and paying my own bills—and I mean actually mystified. One of my roommates asked me to explain to her how I got my money because she honestly couldn’t wrap her mind around the notion that what I had was what I earned, period. She couldn’t imagine my life, although we were sleeping six feet away from each other in bunk beds every night, because her parents provided for her entirely. I envied her at the time, but now I’m grateful I had the experience I did. Growing up poor aged me but it also showed me at a very young age that I could stand on my own two feet. There is nothing more liberating that knowing you can make your own way in the world.
By the time I graduated college, my mom was dead—she died of cancer a few months before, at the age of 45—and that made me feel older too, especially because I was also long-estranged from my father, so from the age of 22 onward I didn’t have parents. I remember walking around the streets of Minneapolis and St. Paul blasting cassette tapes of Suzanne Vega and Shawn Colvin on my Walkman looking at people and wondering if they had a mother, even though I knew the answer. They always had a mother. There was no one who didn’t have a mother but me, or at least it felt that way.
Ever since my mom died, I’ve been afraid I’d die young and getting older heightens my awareness of that...I want more time. I’m not one of those when my time’s up, it’s up people. I want to live! I want to turn 100 and marvel at my children’s gorgeous heads of gray hair.
And it was kind of true—even now, at the age of 54, most of my friends’ moms are still alive. So to be in my 20s and have no parents, it made me feel ancient. It made me feel alone. It made me feel bereft. It made me feel rootless and utterly free. Good things and bad things could happen to me and who would care? I spent a lot of years answering that question.
On top of all that, I got married a month before my 20th birthday. I was a teenage bride! That makes me shake my head now and wonder what the hell I was thinking, though I loved my ex-husband like mad. That’s what I was thinking. Mad young love! When I got divorced at 26 I felt ruined—and distinctly older than other 26-year-olds. Now I look back and all I can see is how young I was.
What do you like about being your age?
Knowing how strong I am. Knowing that I can keep going no matter what, even when it hurts. Fifty-four years of living has taught me that I can persist through the hard times—and also that hard times pass. Life is suffering and life is joy. It’s ugliness and it’s beauty. It’s love and it’s loss. Everyone says this, but it’s true: getting older gives you perspective that you can only get from the passage of time.
I also love this particular decade I’m in because I’m coming to realize that it’s going to be a transformational one for me—one that’s utterly different from my 20s, and yet in some ways similar. My kids are reaching adulthood over these next few years and as I witness them moving into their own lives I’m wondering about where my life is moving too. What will I do in my 60s and beyond? The path ahead feels open in a way it hasn’t for some time.
In my 20s and 30s, I had a vague sense that by my mid-50s I’d have downshifted a bit in my professional life—perhaps my ambitions as a writer would’ve mellowed. But the opposite is true. I feel so energized by my work and my creative life right now. I feel like I’m in my prime.
What is difficult about being your age?
Ever since my mom died, I’ve been afraid I’d die young and getting older heightens my awareness of that. It’s not that I’m anxious about it daily. It doesn’t dominate my life or keep me up at night. But sometimes I’ll do the math and think it can’t be true that in thirty years I’ll be 84! I want more time. I’m not one of those when my time’s up, it’s up people. I want to live! I want to turn 100 and marvel at my children’s gorgeous heads of gray hair.
What is surprising about being your age, or different from what you expected, based on what you were told?
I think I probably thought my life in this decade would be quieter than it is. In my 20s and 30s, I had a vague sense that by my mid-50s I’d have downshifted a bit in my professional life—perhaps my ambitions as a writer would’ve mellowed. But the opposite is true. I feel so energized by my work and my creative life right now. I feel like I’m in my prime.
What has aging given you?
A greater sense of gentleness toward myself and others. I’m less likely to believe the assumptions I’ve made about others are true and more aware that I’ve made assumptions. I see more shades of gray, rather than black and white.
Taken away from you?
I remember that crazy wonderful scary feeling I had in my 20s when it felt like anything could happen. There were so many possibilities, so many paths, and I didn’t know which I would walk. I could be someone who never had children or someone who had six. I could live in Alaska or Paris. I could find love with one partner or hop from one to the next. My life was all questions. I don’t think it’s possible for me to feel that way any longer because I’ve answered a lot of those questions by now with my own life. That doesn’t mean I don’t feel a sense of possibility any longer, but the paths are fewer.
I’m aware that I’m perceived by most people as being less sexually attractive than I used to be. Fewer people flirt with me. Fewer people even glance my way. I can’t say it bothers me. If anything, it’s freeing. I love moving into what I call the crone age.
How has getting older affected your sense of yourself, or your identity?
I’m aware that I’m perceived by most people as being less sexually attractive than I used to be. Fewer people flirt with me. Fewer people even glance my way. I can’t say it bothers me. If anything, it’s freeing. I love moving into what I call the crone age.
What are some age-related milestones you are looking forward to? Or ones you “missed,” and might try to reach later, off-schedule, according to our culture and its expectations?
I’m looking forward to celebrating my 100th birthday in grand style.
What has been your favorite age so far, and why? Would you go back to this age if you could?
My early 40s were a pretty great era because I felt both young and very grown up, but I wouldn’t go back there. I’d never go back.
Is there someone who is older than you, who makes growing older inspiring to you? Who is your aging idol and why?
There are so many older people who inspire me. All the people who stay curious and awake to their own evolution. All the people who keep making things, doing things, connecting and contributing to their communities with loving kindness. I’m particularly inspired by writers who not only keep writing into old age but writing brilliantly. When the New York Times asked me to do a Dear Sugar-esque podcast at the outset of the pandemic I told them I didn’t want to give advice; I wanted to seek wisdom. And for the podcast—which is called Sugar Calling—I sought wisdom from the source I’ve turned to time and time again: great writers. The rule I made is that all the writers I interviewed had to be over the age of 60, though most were over the age of 70 and even 80. I interviewed people whose work I’ve admired for years—writers like Amy Tan, Joy Harjo, Margaret Atwood and Judy Blume (which had the teenager inside of me utterly starstruck). I was so inspired by the stories they shared about how to survive difficult times, how to laugh, and forgive and most of all, to keep writing.
I refuse to by coy about how old I am. So many of us were taught that it’s rude to ask a woman’s age and I reject that entirely. I find it so insulting that I should be reluctant to state one of the most basic facts about myself.
What aging-related adjustments have you recently made, style-wise, beauty-wise, health-wise?
I’ve never done any aesthetic enhancements or interventions like Botox or such, but I do get facials more regularly than I used to. I don’t even know if it makes a difference in my appearance, but I like that feeling of being scrubbed until glow every month or two.
Style-wise, I’ve lately been toying with the idea of adopting a uniform, or at least a fairly limited mix-and-match clothing capsule. I’d rather not spend my dotage wondering what the fuck to wear every damn day.
What’s an aging-related adjustment you refuse to make, and why?
I refuse to be coy about how old I am. So many of us were taught that it’s rude to ask a woman’s age and I reject that entirely. I find it so insulting that I should be reluctant to state one of the most basic facts about myself. I love knowing the year when people were born. It tells you something about the cultural moment, the atmosphere, the music and literature and politics they were steeped in as they grew up.
Of course, I know the reasons why some people don’t want to share their age, but those reasons are rooted in shame, in ageism, in the false stories that are put upon us based on how old we are. The only way to vanquish all that tosh is to tell the truth without apology.
I’m less likely to believe the assumptions I’ve made about others are true and more aware that I’ve made assumptions. I see more shades of gray, rather than black and white.
What’s your philosophy on celebrating birthdays as an adult?
I think one should celebrate birthdays however one wants to at any age.
How do you celebrate yours?
Exactly how you might imagine: with wild abandon.
I love, love, love Cheryl Strayed. Almost 11 years ago I climbed in a hammock and started reading "Wild." My mom had died 4 days earlier. Little did I know her memoir was about her mom dying; I thought it was about hiking the Pacific Crest Trail and her hiking experience (I had always wanted to hike the PCT trail, too). Turns out, we're both from northern Minnesota and my mom died in the exact same hospital where Cheryl's mom died. It was incredible synchronicity, and that book helped me heal in a very difficult time. I read straight through her book in two days, laying in that hammock, crying all the way through. I will always feel like we're soul sisters, though we've never met, of course. The book was so important for me, both in discovering the shared loss of our mothers and also in the desire to explore wild places. It's gratifying to learn she's such a cool person, in addition to being a wonderful writer. And yes, hard times do pass. Thanks for everything you write, Cheryl.
"I'd rather not spend my dotage wondering what the fuck to wear every day." Priceless!